Record Information
Version1.0
Creation date2011-03-17 23:26:04 UTC
Update date2019-11-26 03:20:41 UTC
Primary IDFDB021665
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-alpha-Terpinyl acetate
Description(±)-alpha-terpinyl acetate, also known as P-menth-1-en-8-yl acetate or (±)-α-terpinyl acetic acid, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, (±)-alpha-terpinyl acetate is considered to be an isoprenoid lipid molecule (±)-alpha-terpinyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (±)-alpha-terpinyl acetate is a bergamot, citrus, and herbal tasting compound and can be found in a number of food items such as sweet basil, roselle, cardamom, and mandarin orange (clementine, tangerine), which makes (±)-alpha-terpinyl acetate a potential biomarker for the consumption of these food products (±)-alpha-terpinyl acetate can be found primarily in saliva (±)-alpha-terpinyl acetate exists in all eukaryotes, ranging from yeast to humans.
CAS Number58206-95-4
Structure
Thumb
Synonyms
SynonymSource
p-Menth-1-en-8-yl acetateKegg
p-Menth-1-en-8-yl acetic acidGenerator
a-Terpineol acetateGenerator
a-Terpineol acetic acidGenerator
alpha-Terpineol acetic acidGenerator
Α-terpineol acetateGenerator
Α-terpineol acetic acidGenerator
FEMA 3047HMDB
a-Terpinyl acetateGenerator
a-Terpinyl acetic acidGenerator
alpha-Terpinyl acetic acidGenerator
Α-terpinyl acetateGenerator
Α-terpinyl acetic acidGenerator
(S)-alpha-Terpinyl acetatemanual
(S)-p-Menth-1-en-8-yl acetatemanual
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP4.32ALOGPS
logP2.62ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity57.61 m³·mol⁻¹ChemAxon
Polarizability23.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H20O2
IUPAC name2-(4-methylcyclohex-3-en-1-yl)propan-2-yl acetate
InChI IdentifierInChI=1S/C12H20O2/c1-9-5-7-11(8-6-9)12(3,4)14-10(2)13/h5,11H,6-8H2,1-4H3
InChI KeyIGODOXYLBBXFDW-UHFFFAOYSA-N
Isomeric SMILESCC(=O)OC(C)(C)C1CCC(C)=CC1
Average Molecular Weight196.286
Monoisotopic Molecular Weight196.146329884
Classification
Description belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.43%; H 10.27%; O 16.30%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -79.92DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.4657DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9500000000-ffe7aaa2d3a38a8ed5b8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9500000000-ffe7aaa2d3a38a8ed5b8JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-b8293aa3446037e3fc50JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-3882c1dcf928825bf3baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052k-6900000000-b4a6d18cb758c8c91aa1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1010-9300000000-257ef5e703a03c85b0b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-5359896272e433550068JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-3900000000-5a9af9efd8065cc02e7aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-7900000000-143c587d14b196b024abJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJQJ06-Z:DVY14-S
EAFUS IDNot Available
Dr. Duke IDD-ALPHA-TERPINYL-ACETATE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).